- Decarboxylative Hydroxylation of Benzoic Acids
-
Herein, we report the first decarboxylative hydroxylation to synthesize phenols from benzoic acids at 35 °C via photoinduced ligand-to-metal charge transfer (LMCT)-enabled radical decarboxylative carbometalation. The aromatic decarboxylative hydroxylation is synthetically promising due to its mild conditions, broad substrate scope, and late-stage applications.
- Ritter, Tobias,Su, Wanqi,Xu, Peng
-
p. 24012 - 24017
(2021/10/06)
-
- Process for Preparing Nafamostat Mesilate and Intermediate Thereof
-
The present invention provides a method for efficiently producing astaxmostat mesylate through a simple process and a method for producing 6 - amidino -2 - naphthol mesylate in high yield under mild conditions.
- -
-
Paragraph 0080-0081
(2021/10/27)
-
- A facile and versatile electro-reductive system for hydrodefunctionalization under ambient conditions
-
A general electrochemical system for reductive hydrodefunctionalization is described, employing the inexpensive and easily available triethylamine (Et3N) as a sacrificial reductant. This protocol is characterized by facile operation, sustainable conditions, and exceptionally wide substrate scope covering the cleavage of C-halogen, N-S, N-C, O-S, O-C, C-C and C-N bonds. Notably, the selectivity and capability of reduction can be conveniently switched by simple incorporation or removal of an alcohol as a co-solvent.
- Huang, Binbin,Guo, Lin,Xia, Wujiong
-
supporting information
p. 2095 - 2103
(2021/03/26)
-
- Iodine(III)-Mediated, Controlled Di- or Monoiodination of Phenols
-
An oxidative procedure for the electrophilic iodination of phenols was developed by using iodosylbenzene as a nontoxic iodine(III)-based oxidant and ammonium iodide as a cheap iodine atom source. A totally controlled monoiodination was achieved by buffering the reaction medium with K3PO4. This protocol proceeds with short reaction times, at mild temperatures, in an open flask, and generally with high yields. Gram-scale reactions, as well as the scope of this protocol, were explored with electron-rich and electron-poor phenols as well as heterocycles. Quantum chemistry calculations revealed PhII(OH)·NH3 to be the most plausible iodinating active species as a reactive "I+" synthon. In light of the relevance of the iodoarene moiety, we present herein a practical, efficient, and simple procedure with a broad functional group scope that allows access to the iodoarene core unit.
- Satkar, Yuvraj,Yera-Ledesma, Luisa F.,Mali, Narendra,Patil, Dipak,Segura-Quezada, Luis A.,Ramírez-Morales, Perla I.,Solorio-Alvarado, César R.,Navarro-Santos, Pedro
-
p. 4149 - 4164
(2019/04/30)
-
- C -Glycosylation of Substituted β-Naphthols with Trichloroacetimidate Glycosyl Donors
-
Several glycosyl donors have been systematically investigated for C-glycosylation of substituted β-naphthols to delineate the effect of the substituents. Whereas glycosylations of the parent 2-naphthol are smoothly achievable, those of differently substituted 2-naphthols are cumbersome. Efficiency of the glycosylation depends on the nature of both the glycosyl donors and the substituents of the arene ring. Among various glycosyl donors, trichloroacetimidate glycosyl donors are found to be superior for glycosylation with substituted 2-naphthols.
- Chakraborty, Soumen,Mal, Dipakranjan
-
p. 1560 - 1568
(2018/01/17)
-
- 3-Aryl-1,2,4-oxadiazole Derivatives Active Against Human Rhinovirus
-
The human rhinovirus (hRV) is the causative agent of the common cold that often aggravates respiratory complications in patients with asthma or chronic obstructive pulmonary disease. The high rate of mutations and variety of serotypes are limiting the development of anti-hRV drugs, which emphasizes the need for the discovery of novel lead compounds. Previously, we identified antiviral compound 1 that we used here as the starting material for developing a novel compound series with high efficacy against hRV-A and -B. Improved metabolic stability was achieved by substituting an ester moiety with a 1,2,4-oxadiazole group. Specifically, compound 3k exhibited a high efficacy against hRV-B14, hRV-A21, and hRV-A71, with EC50 values of 66.0, 22.0, and 3.7 nM, respectively, and a relevant hepatic stability (59.6 and 40.7% compound remaining after 30 min in rat and human liver microsomes, respectively). An in vivo study demonstrated that 3k possessed a desirable pharmacokinetic profile with low systemic clearance (0.158 L·h-1·kg-1) and modest oral bioavailability (27.8%). Hence, 3k appears to be an interesting candidate for the development of antiviral lead compounds.
- Kim, Jinwoo,Shin, Jin Soo,Ahn, Sunjoo,Han, Soo Bong,Jung, Young-Sik
-
p. 667 - 672
(2018/05/14)
-
- Methanesulfonic acid the naphthalene not takes charge of he intermediate — 6 - amidino - 2 - naphthol armor sulfonate synthetic method
-
The present invention relates to a new synthesis method for a nafamostat mesylate intermediate 6-amidino-2-naphthol methanesulfonate. According to the new method, 6-hydroxy-2-naphthaldehyde is adopted as a raw material, dimethyl sulfoxide is adopted as a reaction solvent, the dimethyl sulfoxide and hydroxylamine hydrochloride are subjected to an addition elimination reaction to obtain 6-cyano-2-naphthol, the 6-cyano-2-naphthol is subjected to a pinner reaction in a HCl/methanol solution to obtain 6-hydroxy-2-naphthalene imino methyl ester hydrochloride, ammonia gas is introduced to carry out an aminolysis reaction to obtain 6-amidino-2-naphthol, and the 6-amidino-2-naphthol sequentially reacts with sodium bicarbonate and methanesulfonic acid to convert into the 6-amidino-2-naphthol methanesulfonate. According to the present invention, in the new synthesis method, the 6-cyano-2-naphthol preparation in the first step adopts the completely-new method, the use of the highly toxic copper cyanide in the traditional method is avoided, the operations are simple, and the conditions are mild; and the second step adopts the improved pinner method, wherein the reaction of acetyl chloride and methanol is adopted to produce HCl to replace direct introduction of HCl gas into the reaction system, such that the improved method has strong operability and industrialization is easily achieved.
- -
-
Paragraph 0008; 0009
(2017/12/30)
-
- Synthesis and cytotoxicity of n-substituted dibenzo[a,j]xanthene-3,11-dicarboxamide derivatives
-
In order to study the structure-activity relationships of xanthene derivatives, four series of N-substituted 14-aryl-14H-dibenzo[a,j]xanthene-3,11-dicarboxamide derivatives were synthesized. The structures of all compounds were identified by 1H-NMR HR-MS and IR spectra in which compounds 6a-h were further identified by 13C-NMR spectra. The in vitro antitumor activity of the synthesized compounds was tested by MTT assay. Most of them displayed strong inhibitory activity on human hepatocellular carcinoma cell lines (SK-HEP-1 HepG2 and SMMC-7721 cells) and acute promyelocytic leukemia NB4 cells. Compounds 6c-6e exhibited significant inhibitory activity against NB4 cells with IC50 values of 0.52 μM and 0.76 μM respectively much lower than 5.31 μM of the positive control As2O3.
- Song, Yongbin,Yang, Yihui,Wu, Lijun,Dong, Naiwei,Gao, Shang,Ji, Hongrui,Du, Xia,Liu, Bo,Chen, Guoyou,Dembinski, Roman
-
-
- Design, Conformation, and Crystallography of 2-Naphthyl Phenyl Ethers as Potent Anti-HIV Agents
-
Catechol diethers that incorporate a 7-cyano-2-naphthyl substituent are reported as non-nucleoside inhibitors of HIV-1 reverse transcriptase (NNRTIs). Many of the compounds have 1-10 nM potencies toward wild-type HIV-1. An interesting conformational effect allows two unique conformers for the naphthyl group in complexes with HIV-RT. X-ray crystal structures for 4a and 4f illustrate the alternatives.
- Lee, Won-Gil,Chan, Albert H.,Spasov, Krasimir A.,Anderson, Karen S.,Jorgensen, William L.
-
supporting information
p. 1156 - 1160
(2016/12/16)
-
- Emission and transient absorption measurements of substitution effects of C-C triple bonds on relaxation processes of the fluorescent state of naphthalenes
-
Photophysical and photochemical properties of naphthalenes substituted with trimethylsilylethynyl, tert-butylethynyl, and trimethylsilylbutadiynyl groups were investigated by measurement of fluorescence yields, lifetimes, and triplet absorption. Introducing trimethylsilylethynyl and tert-butylethynyl groups to the 1-position of the naphthalene skeleton substantially enhanced fluorescence and intersystem crossing (ISC). The rates of fluorescence of 2-substituted naphthalenes were low. The effect of ethynyl groups on the 1-substituted naphthalenes was rationalized in terms of an increase of the transition moment along the short axis of the naphthalene skeleton. Substitution of the trimethylsilylbutadiynyl group at the 1 or 2-position of the naphthalene skeleton caused a considerable decrease in the fluorescence yield (approximately 0.01) and an increase in the ISC yield (0.99).
- Yamaji, Minoru,Maeda, Hajime,Minamida, Keita,Maeda, Tomohiro,Asai, Kengo,Konishi, Gen-Ichi,Mizuno, Kazuhiko
-
p. 321 - 345
(2013/03/14)
-
- Design and synthesis of laser-activatable tetrazoles for a fast and fluorogenic red-emitting 1,3-dipolar cycloaddition reaction
-
The design and synthesis of a new class of laser light activatable tetrazoles with extended π-systems is reported. Upon 405 nm laser light irradiation, these bithiophene-substituted tetrazoles underwent extremely fast 1,3-dipolar cycloaddition reactions with dimethyl fumarate with second-order rate constants approaching 4000 M-1 s-1. The resulting pyrazoline cycloadducts exhibited solvent-dependent red fluorescence, making these tetrazoles potentially useful as fluorogenic probes for detecting alkenes in vivo.
- An, Peng,Yu, Zhipeng,Lin, Qing
-
supporting information
p. 5496 - 5499
(2013/11/19)
-
- Design, synthesis and anticancer activity of N3,N 11-bis(2-hydroxyethyl)-14-aryl-14H-dibenzo[a,j]xanthenes-3, 11-dicarboxamide
-
A series of novel N3,N11-bis(2-hydroxyethyl)-14-aryl- 14H-dibenzo[a,j]xanthenes-3,11-dicarboxamide, three N3,N 11-bis(2-hydroxyethyl)-14-aryl-14H-dibenzo[a,j]xanthene-3, 11-dimethanamine derivatives and their intermediates 14-aryl-14H-dibenzo[a,j] xanthenes-3,11-dicarboxylic acid, were synthesized, and the structures of which were characterized by 1H-NMR, 13C-NMR, high resolution (HR)-MS, and IR spectra. The antitumor activities of these molecules were evaluated on five cancer cell lines. The results of in vitro assay against human hepatocellular carcinoma cell lines (SK-HEP-1 and HepG2 and SMMC-7721 cells), acute promyelocytic leukemia NB4 cells and uterine cervix cancer HeLa cells, show several compounds to be endowed with cytotoxicity in micromolar to submicromolar range. The carboxamide derivatives 6c and 6e exhibitted good inhibition on NB4 cancer cells, and the IC50 values of which were 0.82 μm and 0.96 μm, respectively, much lower than 5.01 μm of the positive control As2O3. Flow cytometric analysis results revealed that compounds 6e and 6f may induce tumor cell apoptosis.
- Song, Yongbin,Yang, Yihui,You, Jun,Liu, Bo,Wu, Lijun,Hou, Yunlong,Wang, Wenji,Zhu, Jiuxin
-
p. 167 - 175
(2013/03/28)
-
- Acid-catalyzed dehydration of naphthalene-cis-1,2-dihydrodiols: Origin of impaired resonance effect of 3-substituents
-
Acid-catalyzed dehydrations of substituted naphthalene-cis-1,2-dihydrodiols occur with loss of the 1- or 2-OH group to form 2- and 1-naphthols, respectively. Effects of substituents MeO, Me, H, F, Br, I, and CN at 3-, 6-, and 7-positions of the naphthalene ring are consistent with rate-determining formation of β-hydroxynaphthalenium ion (carbocation) intermediates. For reaction of the 1-hydroxyl group the 3-substituents are correlated by the Yukawa-Tsuno relationship with ρ = -4.7 and r = 0.25 or by σp constants with ρ = -4.25; for reaction of the 2-hydroxyl group the 3-substituents are correlated by σm constants with ρ = -8.1. The correlations for the 1-hydroxyl imply a surprisingly weak resonance interaction of +M substituents (MeO, Me) with a carbocation reaction center but are consistent with the corresponding correlation for acid-catalyzed dehydration of 3-substituted benzene-cis-1,2-dihydrodiols for which ρ = -6.9 and r = 0.43. Substituents at the 6- and 7-positions of the naphthalene rings by contrast are correlated by σ+ with ρ = -3.2 for reaction of the 1-hydroxyl group and ρ = -2.7 for reaction of the 2-hydroxyl group. The unimpaired resonance implied by these substituent effects appears to be inconsistent with a previous explanation of the weak resonance of the 3-substituents in terms of imbalance of charge development and/or nonplanarity of the benzenium ring in the transition state. An alternative possibility is that the adjacent hydroxyl group interferes sterically with conjugation of +M substituents. "Hyperaromaticity" of the arenium ion intermediates does not appear to be a factor influencing this behavior.
- Kudavalli, Jaya Satyanarayana,Boyd, Derek R.,Sharma, Narain D.,More O'Ferrall, Rory A.
-
supporting information; experimental part
p. 9338 - 9343
(2012/01/03)
-
- Synthesis and anti-HIV activity of 2-naphthyl substituted DAPY analogues as non-nucleoside reverse transcriptase inhibitors
-
Nine newly 6-cynao-2-naphthyl substituted diarylpyrimidines (DAPY) were synthesized as non-nucleoside reverse transcriptase inhibitors on the basis of our previous work. The antiviral and cytotoxicity evaluation indicated that these compounds displayed strong activity against wild-type HIV-1 at nanomolar concentrations with selectivity index SI greater than 23 779. The most active compounds 3c and 3e exhibited activity against the double mutant (103N+181C) strains at an EC50 of 0.16 and 0.15 μM, and were more activity than that of efavirenz.
- Liang, Yong-Hong,He, Qiu-Qin,Zeng, Zhao-Sen,Liu, Zhi-Qian,Feng, Xiao-Qing,Chen, Fen-Er,Balzarini, Jan,Pannecouque, Christophe,Clercq, Erik De
-
experimental part
p. 4601 - 4605
(2010/08/06)
-
- Enhanced O-dealkylation activity of SiCl4/LiI with catalytic amount of BF3
-
Dibenzyloxydihydrobenzoxathiin 1, which resisted debenzylation with SiCl4/LiI, was effectively debenzylated with SiCl4/LiI in the presence of a catalytic amount of BF3. The HCl salt of the bis-debenzylated product 2 was isolated in 90% yield and 99% purity. This enhanced dealkylation activity has also been observed with other substrates.
- Zewge, Daniel,King, Anthony,Weissman, Steven,Tschaen, David
-
p. 3729 - 3732
(2007/10/03)
-
- Naphthamidine urokinase inhibitors
-
Compounds having the formula: are inhibitors of urokinase and are useful in the treatment of diseases in which urokinase plays a role. Also disclosed are urokinase-inhibiting compositions, methods for the preparation of urokinase-inhibitors, and a method of inhibiting urokinase in a mammal.
- -
-
-
- Naphthamidine urokinase inhibitors
-
Compounds having the formula are inhibitors of urokinase and are useful in the treatment of diseases in which urokinase plays a role. Also disclosed are urokinase-inhibiting compositions, methods for the preparation of urokinase-inhibitors, and a method of inhibiting urokinase in a mammal.
- -
-
-
- NAPHTHALENE AMIDES HAVING LEUKOTRIENE-ANTAGONISTIC ACTION
-
Naphthalene amides of formula (I) wherein the substituent containing A is bound to the 6- or 7- position of the 2-naphthol system; the substituent containing B is bound to the benzene ring at any free position; R is hydrogen or methyl; R is hydrogen, fluorine, chlorine or -OCH3, which is bound to the naphthalene system at any positions except the 2- and the one occupied by the other substituent; R is hydrogen, fluorine, chlorine or bromine; A- is -CO-NR- or -NR-CO- group, wherein R is hydrogen or methyl; B is a 5-tetrazolyl or -COOR group, wherein R is hydrogen, a (C1-C4)-alkyl or a phenylalkyl group of less than 10 carbon atoms; m is 0 or 1; n and p are integers from 0 to 6, with the proviso that n + p is less or equal to 6; as well as the solvates and pharmaceutically acceptable salts thereof, have leukotriene antagonistic action.
- -
-
-
- Sulfonamide bridging compounds that inhibit tryptase activity
-
The present invention is directed to compounds which are capable of inhibiting the activity of tryptase. Such compounds are useful in the treatment or prevention of inflammatory disease, particularly those disease states which are mediated by mast cell activation. Also encompassed by the invention are formulations comprising the noted compounds, processes for preparing such compounds and methods for treating or preventing an inflammatory disease.
- -
-
-
- Urokinase inhibitors
-
Compounds having the formula are inhibitors of urokinase and are useful in the treatment of diseases in which urokinase plays a role. Also disclosed are urokinase-inhibiting compositions and a method of inhibiting urokinase in a mammal.
- -
-
-
- Ukokinase inhibitors
-
Compounds having the formula are inhibitors of urokinase and are useful in the treatment of diseases in which urokinase plays a role. Also disclosed are urokinase-inhibiting compositions and a method of inhibiting urokinase in a mammal.
- -
-
-
- Synthesis, transition temperatures, and optical properties of various 2,6-disubstituted naphthalenes and related 1-benzothiophenes with butylsulfanyl and cyano or isothiocyanato terminal groups
-
Fourteen compounds based on 2,6-disubstituted naphthalenes or related 1-benzothiophene moieties with butylsulfanyl and cyano or isothiocyanato terminal groups have been synthesised. The transition temperatures of the compounds and their refractive indices have been determined and the derived values for the optical anisotropies, polarisabilities and order parameters have been calculated. With one exception (which also shows a smectic A phase), all the compounds with naphthyl and phenyl groups are solely nematogenic; for these compounds the naphthyl unit gives an average increase in T(N-I) value and melting point of 72 and 20°C respectively compared to the values for the compounds with a phenyl in place of the naphthyl unit. The incorporation of a 2,5-thiophene unit in place of phenyl lowers T(N-I) and when it is part of a 1-benzothiophene unit the depression is even greater. The naphthalene compounds increase the values of optical anisotropy by approximately 0.04, compared to the phenyl systems, mainly because they increase the refractive index of the e-ray (n values); compound 12 has an exceptionally high optical anisotropy (Δn value) of 0.54.
- Seed,Toyne,Goodby,Hird
-
p. 2069 - 2080
(2007/10/03)
-
- Preparation and pharmacological evaluation of novel glycoprotein (Gp) IIb/IIIa antagonists. 1. The selection of naphthalene derivatives
-
The synthesis and design using molecular modeling techniques for non- peptide, low molecular weight novel fibrinogen receptor (glycoprotein IIb/IIIa: Gp IIb/IIIa) antagonists, is reported. We used a highly potent serine protease inhibitor, Nafamostat, having an amidinonaphthyl unit as the starting compound. The compounds 4-(6-amidino-2- naphthylaminocarbonyl)phenoxyacetic acid (5a) and 4-(6-amidino-2- naphthalenecarboxamido)phenoxyacetic acid (5b) inhibited adenosin-5'- diphospate (ADP)-induced aggregation of human platelet-rich plasma (PRP) with IC50 values of 0,05 and 0.07 μM, respectively, and had lost their ability to inhibit a variety of serine proteases, including thrombin, factor Xa, plasmin and trypsin.
- Ono, Shin'ichiro,Inoue, Yoshihisa,Yoshida, Tomohiro,Ashimori, Atsuyuki,Kosaka, Keigo,Imada, Teruaki,Fukaya, Chikara,Nakamura, Norifumi
-
p. 1685 - 1693
(2007/10/03)
-
- Cyclic imino derivatives and pharmaceutical compositions containing them
-
The invention relates to cyclic imino compounds which have, inter alia, valuable pharmacological properties, especially inhibitory effects on cell aggregation, pharmaceutical compositions which contain these compounds and processes for preparing them.
- -
-
-
- Syntheses and biological evaluation of two new naproxen analogs
-
Reported herein are the syntheses and biological activities of two structural analogues (2 and 3) of naproxen (1).
- Jung, Kyung Woon,Janda, Kim D.,Sanfilippo, Pauline J.,Wachter, Michael
-
p. 2281 - 2282
(2007/10/03)
-
- Photoexcited proton transfer from enhanced photoacids
-
Naphthols with electron-withdrawing groups such as cyano or methanesulfonyl at C-5 and C-8 exhibit greatly enhanced photoacidity. This increase in photoacidity enables the substituted naphthols to undergo excited-state proton transfer (ESPT) in alcohols and Me2SO in the absence of water. In aqueous tetrahydrofuran solution, efficient proton transfer to water occurs at much lower water concentrations than with the parent naphthol, and the kinetics of proton transfer indicate that a smaller water cluster is involved.
- Tolbert, Laren M.,Haubrich, Jeanne E.
-
p. 10593 - 10600
(2007/10/02)
-
- Liquid crystal compounds and compositions
-
Liquid crystal naphtalene compounds, represented by the following formula (1) are disclosed. R-Z-A-NAP-Z?-R? (1)In the formula (1), R is an alkyl group containing 1 to 18 carbon atoms; R? is an alkyl group containing 1 to 21 carbon atoms; NAP represents 2,6-naphthylene group; A, Z and Z? are as follows: 1) A is Pyr> and (a) Z is - or and Z? is O, or (b) Z is - and Z? is COO; 2) if A is Pym>, (a) Z is - and Z? is O, or (b) Z is O and Z? is -, O or ; 3) A is FPhF and (a) Z is - or O and Z? is -, O or COO, (b) Z is OCO and Z? is - or O, or (c) Z is and Z? is O; 4) A is PhF and (a) Z is - or and Z? is O, (b) Z is O and Z? is -, or (c) Z is - and Z? is COO; 5) A is FPh and (a) Z is O and Z? is-, (b) Z is -, O, or OCO and Z? is O, or (c) Z is O and Z? is COO; 6) A is Pyr and Z is -, O or and Z? is O; or 7) A is Ph and one of Z and Z? is - and the other is O; As a component of liquid crystal compositions showing chiral smectic C phase, these compounds can provide liquid crystal compositions of improved orientation and free from zigzag deffects, and liquid crystal display elements of high contrast ratio.
- -
-
-
- SYNTHESIS OF 6,7-SUBSTITUTED 2-NAPHTHOLS
-
6,7-Substituted 2-naphthols were obtained with 52-70percent yields by the condensation of the benzoate or acetate of α,α,α',α'-tetrabromo-3,4-xylenol with various dienophiles, followed by hydrolysis of the obtained esters.
- Kopranenkov, V. N.,Makarova, E. A.,Luk'yanets, E. A.
-
p. 303 - 306
(2007/10/02)
-
- Liquid crystalline materials
-
Novel liquid crystal materials which are trans-4-alkylcyclohexane-1-carboxylic acid esters are provided having the general formula: STR1 where R is a normal or branched chain alkyl group, which may also contain a chiral center, containing up to ten carbon atoms and X is selected from the groups: STR2 where A is a cyano group, a normal or branched chain alkyl group, which may also contain a chiral center, containing up to ten carbon atoms or an alkoxy group in which the alkyl group is as defined immediately above, and where Y is a halogen, preferably chlorine, or hydrogen.
- -
-
-
